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How One Customer Interview Completely Transformed This Startup's Trajectory

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Manage episode 454079973 series 3413708
Content provided by Dani Woolf. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Dani Woolf or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://ppacc.player.fm/legal.

The art of successful startups isn't just in building the right product—it's in listening, pivoting, and solving real problems.

In this episode of Audience 1st Podcast, I sat down with James Farrow, co-founder of Cyft, to explore the intricate dance of startup growth, MSP market demands, and the mindset shifts required for success.

We covered everything from Cyft’s pivot from the MDR market to MSPs, to how a single user interview transformed the company’s trajectory.

James opened up about the emotional and operational challenges of building a startup, including how personal relationships fuel professional growth.

He also shared his mental models for approaching complex decisions, including first-principles thinking and inversion, and gave a glimpse into what’s next for Cyft as they scale their offerings.

This conversation is one of the more raw episodes I've had with a special guest, insightful, and packed with actionable advice for anyone building a business, especially in B2B tech.

Whether you’re pivoting, scaling, or just trying to stay true to your mission, James’ journey is a blueprint for thoughtful growth.

  continue reading

98 episodes

Artwork
iconShare
 
Manage episode 454079973 series 3413708
Content provided by Dani Woolf. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Dani Woolf or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://ppacc.player.fm/legal.

The art of successful startups isn't just in building the right product—it's in listening, pivoting, and solving real problems.

In this episode of Audience 1st Podcast, I sat down with James Farrow, co-founder of Cyft, to explore the intricate dance of startup growth, MSP market demands, and the mindset shifts required for success.

We covered everything from Cyft’s pivot from the MDR market to MSPs, to how a single user interview transformed the company’s trajectory.

James opened up about the emotional and operational challenges of building a startup, including how personal relationships fuel professional growth.

He also shared his mental models for approaching complex decisions, including first-principles thinking and inversion, and gave a glimpse into what’s next for Cyft as they scale their offerings.

This conversation is one of the more raw episodes I've had with a special guest, insightful, and packed with actionable advice for anyone building a business, especially in B2B tech.

Whether you’re pivoting, scaling, or just trying to stay true to your mission, James’ journey is a blueprint for thoughtful growth.

  continue reading

98 episodes

All episodes

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In this episode of Audience 1st Podcast, Dani Woolf sits down with Val Popke to explore the unspoken human dimensions of cybersecurity leadership. Val, a veteran, assurance leader, and self-described “Wandering Cyber Vulva,” challenges the industry’s prevailing narratives around hiring, communication, inclusion, and resilience. The discussion goes beyond traditional security frameworks to uncover the cognitive and cultural risks impacting practitioners at all levels. Listeners will walk away with a deeper understanding of why burnout, disconnect, and distrust are systemic, not personal, and how security leaders must evolve to lead in environments of increasing complexity, diversity, and psychological strain. Key Themes: Why psychological safety and cognitive clarity are prerequisites for functional security operations. How the industry’s hidden majority is misaligned with traditional corporate norms and what needs to change. The mismatch between capability and visibility in how cyber professionals are evaluated and excluded. A linguistic and philosophical reframe that emphasizes collaborative understanding over performative inclusion. Why many security professionals are forced to protect their organizations from internal dysfunction while defending against external threats. Trust, mission, and why so many veterans find a natural home in cyber until corporate incentives erode that foundation. Subscribe & Follow: Follow Audience 1st wherever you get your podcasts Connect with Dani Woolf on LinkedIn Learn more about CyberSynapse and qualitative buyer research…
 
What does it really take to secure applications across a hybrid, multi-cloud environment? In this episode of Audience 1st, I sit down with Adolfo Lopez, Sales Engineer at AlgoSec, who brings a practitioner’s lens to the cloud security conversation. From his experience as a network engineer to helping organizations operationalize cloud security today, Adolfo walks us through what most teams overlook—and how to get it right. We cover: Why visibility into application flows is foundational for multi-cloud security What enterprises miss when they treat the cloud like a lift-and-shift extension of on-prem Why security must be application-centric—not infrastructure-led The critical role of policy discovery, orchestration, and automation How AlgoSec ACE helps teams answer the question: “What will break if I make this change?” If your team is working across AWS, Azure, GCP, and on-prem—and struggling to manage risk, connectivity, and policy alignment, this episode breaks it down practically and tactically. To get a demo of AlgoSec, visit: https://www.algosec.com/lp/request-a-demo…
 
In this provocative and no-fluff episode of Keyboard Samurai, host, Wil Kluv, sits down with Dani Woolf and Ben Siegel to unpack what’s broken in how cybersecurity vendors go to market and how to fix it using real buyer data and a deeper understanding of human psychology. Dani and Ben, co-founders of CyberSynapse and veterans of cybersecurity GTM, break down why so many tech marketers are stuck in echo chambers, how pressure from investors leads to safe (but disconnected) strategies, and why most teams are making decisions without actual buyer validation. They explore the psychological barriers to change, why the “herd mentality” is sabotaging innovation, and how to replace opinion with evidence through first-party qualitative research. They also take on the traditional analyst model, offering sharp critique and a more human, scalable alternative rooted in community-sourced insight.…
 
Most vendors won’t admit this, but we will: Your brand doesn’t have a messaging problem. It has a presence problem. And it’s why buyers leave RSA feeling numb, unseen, and unready to trust you. In this episode, Dani Woolf sits down with Zachary Hyde, someone she doesn’t always agree with, which makes this conversation one of the most honest and urgent before a major conference. Together, they break down why most GTM teams think they’re being empathetic but are actually performing a buyer-first fantasy while still clinging to control. If you're showing up to RSA Conference this year with a booth, a badge, and a team under pressure to "drive pipeline" - this is your mirror. Listen before you land in SFO. What We Cover: Why vendors fail to empathize with buyers at conferences How canned “empathetic marketing” actually erodes trust Why emotional presence is a muscle to be consistently massaged The difference between tone-matching and real psychological safety Red flags buyers spot immediately and won’t tell you about What to do this week to actually build trust at RSA (no fluff, no fake discovery)…
 
In this episode of Audience 1st Podcast, Dani sits down with Kristin Demoranville, CEO of Anzen Sage and host of the Bites & Bytes podcast, to uncover the hidden vulnerabilities in one of the world’s most overlooked critical infrastructure sectors: food and agriculture. From insider threats in peanut processing to cyber attacks that disrupt egg supply chains, Kristin breaks down why OT security in food systems isn’t just about uptime, it’s about human lives, brand trust, and national resilience. She pulls no punches, sharing raw stories from the frontlines: Why cybersecurity leaders in food facilities are flying blind What happened when nobody spoke up at Boar’s Head How misinformation campaigns are now a cyber risk vector Why “brown cows make chocolate milk” isn’t just a joke—it’s a symptom of a dangerous knowledge gap We also unpack: The behavioral blind spots holding back executive buy-in Why empathy, not just engineering, is the key to securing food systems What must change in the next 5 years to avoid preventable tragedies…
 
Everyone in tech is suddenly “building community.” But most aren’t building anything close to the real thing - community that's built on mission, trust, and transparency. In this raw, no-buzzword conversation recorded live at CyberMarketingCon, Dani Woolf sits with Ben Siegel, George Kamide, Bronwen Hudson, and Elliot Volkman, real community builders, to unpack what community actually means, why most efforts fall flat, and what it takes to build something alive, resilient, and trustworthy - especially in an industry like cybersecurity where trust is scarce and attention is fractured. We go deep on: Why most corporate “communities” are poorly disguised funnels The difference between an audience, a user group, and a true community What trust looks like when your members are CISOs, not consumers Why growth is nonlinear, unpredictable, and absolutely not guaranteed The emotional labor and invisible moderation that holds real communities together You’ll also hear tactical advice on how to build thriving spaces across Reddit, Slack, LinkedIn, and beyond - without flashy tools or six-figure budgets.…
 
Multi-cloud security isn’t just a technology challenge—it’s an organizational mindset problem. Security teams are juggling AWS, Azure, and GCP, each with different security models, policies, and rules. The result? Silos, misconfigurations, and security gaps big enough to drive an exploit through. In this episode, I sat down with Gal Yosef from AlgoSec to break down: Why multi-cloud security is so complex (and what security teams are getting wrong) How to bridge the gap between network security and cloud security teams How large enterprises manage cloud security policy enforcement across business units The shift from one-size-fits-all security policies to flexible, risk-based guardrails Why automation and visibility are critical for securing multi-cloud environments If you want to secure application connectivity across your hybrid environment, visit algosec.com .…
 
In this episode of Audience 1st, Dani Woolf cuts straight through the noise to confront the silent killer of growth in B2B organizations: misdiagnosing the real growth problem. Most GTM teams think they’re aligned. They’re not. Most believe they’re solving the right thing. They aren’t. In this raw, unfiltered solo episode, Dani unpacks why internal alignment is often a lie, how companies waste entire quarters solving surface-level symptoms, and what it takes to actually identify the bleeding neck - the one problem that’s quietly draining your growth, budget, and team morale. If you’ve ever felt like your team is moving fast but going nowhere, this is the episode you didn’t know you needed. What You’ll Learn: Why most organizations aren’t solving their biggest growth problem and how to tell if you’re one of them The high cost of chasing lagging indicators instead of root causes The real reason marketing, sales, and product don’t align and why buyer truth is the only fix How to recognize “growth triggers” that signal it’s time to do qualitative buyer research Dani’s four-step clarity framework: Diagnose → Validate → Align → Act How to stop guessing, and finally build from buyer reality—not internal theory Don’t just walk away from this episode inspired. Take action. Ask yourself: What’s the one growth problem we think we’re solving right now? Who told us that? When was the last time we heard it from a buyer’s mouth verbatim? What would it feel like to know we’re solving the right thing? If you’re ready to stop guessing and start listening, reach out to Dani and her team . Let’s uncover the bleeding neck together.…
 
In this episode of Audience 1st Podcast, Dani Woolf sits down with Jason Loomis, Chief Information Security Officer at Freshworks, to uncover the raw truth behind how CISOs evaluate security vendors, what actually moves a deal forward, and why most POVs fall flat before they even start. Jason gets brutally honest about the emotional dynamics of enterprise buying, the real reason vendors lose trust, and what it actually takes to turn a POV into a purchase. If you’re in product marketing, sales, or demand generation at a cybersecurity company, this episode will change how you think about the buyer journey and give you a blueprint to win trust, increase conversions, and build long-term influence with technical buyers. What You’ll Learn in This Episode: Why emotional certainty - not ROI - is the key to winning a CISO’s trust The most common POV mistakes vendors make (and how to avoid them) How Jason evaluates vendors - and what gets them instantly disqualified The danger of relying on generic “What problems are you solving?” questions Why transparency beats feature-stuffing in every sales motion How to make your booth presence less awkward and more effective The impact of new SEC regulations on security budgeting and priorities Why buyers referring your product - even after saying no - is the ultimate win If you’re serious about understanding what really drives buyer decisions in cybersecurity subscribe to Audience 1st Podcast. New episodes every week. Raw, unfiltered, and straight from the source - your buyers. 🎧 Listen now, take notes, and share with your GTM team.…
 
In this episode of Risk & Real, host Jeffrey Wheatman sits down with Dani Woolf, co-founder of CyberSynapse and CEO of Audience 1st, to discuss a major shift happening in the cybersecurity industry: the decline of the traditional analyst model and the rise of direct buyer engagement. Cybersecurity vendors that engage directly with their buyers gain faster, more actionable insights than those relying solely on traditional analyst firms. Tune in as we discuss: The flaws in the traditional analyst model and why it’s no longer aligned with today’s fast-moving cybersecurity landscape. Why analyst reports take too long to produce and how they filter buyer insights. The power of direct buyer engagement and how vendors can gather real-time, unfiltered insights. Why cybersecurity vendors are cutting back on analyst firm budgets and shifting to a hybrid research model. How CyberSynapse enables vendors to talk directly to security practitioners, CISOs, and IT leaders. Resources & Links: Learn more about CyberSynapse: https://www.cybersynapse.io Follow Dani Woolf on LinkedIn: https://www.linkedin.com/in/daniwoolf Check out Audience 1st Podcast: https://audience1st.fm Subscribe & Stay Connected! Follow Risk & Real on Apple Podcasts, Spotify, or your favorite podcast app. Connect with host Jeffrey Wheatman on LinkedIn: https://www.linkedin.com/in/jeffreywheatman Don’t forget to leave a review if you enjoyed the episode!…
 
Cloud security didn’t make life easier—it made it exponentially harder. Security teams are stuck in legacy network security models while trying to secure cloud-native applications, security groups, IAM policies, and ephemeral workloads. The result? Confusion, misalignment, and a security posture that can’t keep up with cloud speed. In this episode of Audience 1st Podcast, I chatted with Kyle Wickert from AlgoSec about: Why network security teams struggle with cloud security models The hidden complexity of securing applications across multi-cloud environments Why firewalls and network segmentation don’t translate well to the cloud How security teams can gain visibility and control over cloud security policies The role of automation in bridging the gap between network security and cloud security If you want to secure application connectivity across your hybrid environment, visit algosec.com .…
 
What happens when you meet a cybersecurity founder over dinner and 12 hours later, they’re on your podcast? You get one of the most brutally honest conversations about mobile security. In this episode, Rocky Cole, co-founder of iVerify, lays out why mobile security is dangerously behind—and why businesses are in denial about the scale of the threat. We dive into: The biggest myth in mobile security—why MDM (Mobile Device Management) is not a security tool and never was. Why enterprise security leaders are still ignoring mobile security (even when businesses are now prime targets). How attackers have outpaced traditional mobile security measures—and what needs to change. The operational bottlenecks holding CISOs back from fixing the problem—and how to work around them. Rocky shares raw insights from the frontlines of mobile security, including how his team uncovered new Pegasus infections, why BYOD security is broken, and what companies should be doing NOW. If you're still treating mobile devices differently than desktops, this episode will change your perspective—fast.…
 
Welcome to the first episode of The Confident Cyber Marketer, a monthly series hosted by CyberSynapse.io! In this special in-person episode from New York City, I'm joined by Ben Siegel to break down how cybersecurity marketers and sales teams can accelerate speed to buyer insights to gain a competitive edge. In this tactical, no-BS conversation, we reveal why traditional analyst models fail, why most cybersecurity vendors get it wrong, and how real-time insights from buyers—not just customers—can drive better messaging, faster sales cycles, and higher conversion rates. Key Takeaways and Topics Covered: Why cybersecurity marketing is broken—and how to fix it The myth of proprietary data in cybersecurity marketing Why most data doesn’t tell you the full buyer story The Rapid Buyer Insight Loop (RBIL) framework for gathering and applying insights in less than two weeks The difference between customer research vs. buyer research—and why both matter How traditional analyst models hold cybersecurity vendors back Real-world stories from Dani & Ben on how shifting to direct buyer insights changed everything How to operationalize fast, actionable insights across marketing, sales, and product Metrics that matter: Time to Insight, Time to Decision, Time to Value The high cost of getting your target audience wrong—and how to avoid it. Resources & Links: 🔗 CyberSynapse – Ready to ditch the traditional analyst model and get real insights from real key decision-makers? Visit CyberSynapse.io to schedule a quick call. 🔗 Connect with Dani & Ben – Let’s keep the conversation going! Find us on LinkedIn: Dani Woolf Ben Siegel Don’t forget to subscribe, share, and leave a review if you found this episode valuable. More deep dives into cybersecurity marketing that actually works coming soon!…
 
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Early in my career as a tech marketer, I was told that securing a top-right position in an analyst report was the way to gain credibility. It didn’t take long before I started questioning the whole system. In this episode of Audience 1st, I sat down with Chase Cunningham, VP of Security Market Research at G2 and Co-Founder of Demo-Force, to dig into a hot topic: The flaws in the legacy analyst model and what a modern, buyer-centric approach to market intelligence looks like. We explored how the legacy analyst firms operate, the influence of vendor dollars on rankings, and why many CMOs are quietly walking away from the old system. Chase shared eye-opening insights into how buyers actually evaluate security solutions—hint: they’re relying more on peer reviews and real-world data than on Magic Quadrants. Key takeaways from this episode: Why vendors are overpaying for analyst influence instead of listening to buyers. How data-driven insights from G2 are reshaping go-to-market strategies. The most overlooked buyer signals that vendors should start paying attention to. The shift from C-suite-targeted sales to winning over the “lieutenants” who make buying decisions. The real truth about security software pricing, discounts, and contract lengths. If you're in cybersecurity marketing, product, or sales and looking for smarter ways to understand and reach your buyers, this episode is a must-listen. Get free access to more than 100 million people researching, comparing, and buying software on G2 every year: https://sell.g2.com/…
 
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